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Issue 75, 2014
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Engineering exceptionally strong oxygen superbases with 1,8-diazanaphthalene di-N-oxides

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Abstract

DFT calculations revealed that 1,8-diazanaphthalene di-N-oxides provide extraordinary oxygen superbases, whose gas-phase and acetonitrile basicities surpass those of classical naphthalene-based nitrogen proton sponges. Such high basicity is almost entirely a consequence of a large strain-induced destabilization in neutral forms, while only a small contribution is offered by the intramolecular [O–H⋯O] hydrogen bonding upon protonation.

Graphical abstract: Engineering exceptionally strong oxygen superbases with 1,8-diazanaphthalene di-N-oxides

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Publication details

The article was received on 04 Jul 2014, accepted on 29 Jul 2014 and first published on 29 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC05125D
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 10941-10944
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    Engineering exceptionally strong oxygen superbases with 1,8-diazanaphthalene di-N-oxides

    I. Despotović and R. Vianello, Chem. Commun., 2014, 50, 10941
    DOI: 10.1039/C4CC05125D

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